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Synfacts 2010(8): 0879-0879
DOI: 10.1055/s-0030-1257845
DOI: 10.1055/s-0030-1257845
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
One-Step Synthesis 3-Nitroisoxazoles
Y. A. Volkova, E. B. Averina*, Y. K. Grishin, P. Bruheim, T. S. Kuznetsova, N. S. Zefirov
Lomonosov Moscow State University, Russia; Norwegian University of Science and Technology, Trondheim, Norway
Further Information
Publication History
Publication Date:
22 July 2010 (online)
Significance
Reported is a general method for the synthesis of 3-nitroisoxazoles by reacting activated (Et3N) tetranitromethane with various α,β-unsaturated compounds containing an electron-withdrawing group. Thus, α,β-unsaturated ketones, aldehydes, carboxylic acid esters, amides, and nitroalkenes were all successfully reacted to form the corresponding substituted 3-nitroisoxazoles. The substrate scope was well studied and the yields range from poor to good. The least succesful reaction was that with acrylic amides, which in six out of seven examples led to mixtures of isoxazole and Michael addition products (A and B, respectively).